Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety.
Target compounds 4a- n were obtained by the reaction of 1-substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaldoximes (3) with chloromethylated heterocyclic compounds (ClCH 2-R 3) under reflux conditions in ethanol. Subsequently, the oxidation of 4a- e with KMnO 4 in HOAc at room temperature afforded eight new compounds, 5a- h. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were confirmed by IR, (1)H NMR, (13)C NMR, and elemental analysis. The bioassay revealed that the compounds possessed antiviral activities. It was found that title compounds 4a and 4g had the same inactivation effects against TMV (EC 50 = 58.7 and 65.3 microg/mL) as the commercial product Ningnanmycin (EC 50 = 52.7 microg/mL). To the best of our knowledge, this is the first report on the antiviral activity of pyrazole derivatives containing an oxime moiety.
Ouyang
Guiping
G
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, People's Republic of China.
Cai
Xue-Jian
XJ
Chen
Zhuo
Z
Song
Bao-An
BA
Bhadury
Pinaki S
PS
Yang
Song
S
Jin
Lin-Hong
LH
Xue
Wei
W
Hu
De-Yu
DY
Zeng
Song
S
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D010091:Oximes / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D014027:Tobacco Mosaic Virus / Q000187:drug effects
D000998:Antiviral Agents; D010091:Oximes; D011720:Pyrazoles; C031280:pyrazole